A Proposal Story: This Couple RACED to Get the Engagement Ring—And Won!

When Brittany heard about another girl winning her engagement ring in the Michael C. Fina Diamond Dash, she immediately got busy on Google. She and her boyfriend, Kevin, were ready to get engaged, but they didn't have a ring yet, so why NOT win one? (Not that you NEED a ring to get engaged, but let's not begrudge a girl for wanting one!)

Unfortunately for Brit, there was zero information on the Diamond Dash online, so she tried the usual methods of Internet stalking: setting a Google alert, liking the jeweler on Facebook, following them on Twitter, even emailing them directly, and ... nothing. "I was disappointed," she said, "but I moved on."

So you can imagine her surprise when her daily Gilt email popped into her inbox a few weeks later, and one of the deals was a $60 for a voucher to enter the Michael C. Fina Diamond Dash, with $40 of the cost going toward cancer research. Pretty sweet.

Brittany called Kevin and asked if he was down for the Diamond Dash. "He said he loved my enthusiasm—and that it sounded crazy!" she remembers. "Then he asked me two questions: 'What do YOU think?' I replied, 'I think it's romantic.' And 'How much does it cost to enter?' When I told him $60, he said, 'DONE! Let's do it and WIN!'" So Brittany used $60 of the last $70 in her checking account to buy a voucher. "It was the best $60 I ever spent!" she says.

Kevin later told Brittany that her "romantic" answer is what sold him. "He loved that I didn't say I wanted to do it because I needed an expensive ring, or that we HAD to do it."

After buying the voucher they didn't know if they were definitely in—only 500 couples would get to compete—but a few days later, Brittany got the email confirming that they were one of the lucky 500.

"When I called Kevin I was crying and out of breath! He thought I got mugged!"

Less than two weeks later, they joined the other couples for the start of the scavenger hunt at a comedy club in Times Square, where each couple was given a paper with clues that would lead them to 20 NYC landmarks. At each landmark there would be a person with a Michael C. Fina sign and a code to text to receive one letter of an anagram. The couples would get a point for each landmark they found and a point for solving the anagram.

The next four hours looked like this:

As Brittany and Kevin got some hits—and some misses.

"A lot of the answers I knew randomly," remembers Brittany. "Like one for The Algonquin Hotel, that I recognized from watching a special on cats on Animal Planet." LOL!

When the contest ended at 2 p.m., they had made it to 13 of 20 landmarks and solved the anagram, which was enough points to land them in the top three couples.

(Side story: While chatting with other couples before the top three were announced, they met another couple who decided halfway through Diamond Dash that they didn't want to get married. So they spent the afternoon at a bar!)

Brittany and Kevin had to figure out ONE more landmark AND beat two other couples there to get the ring. They planned to figure out there answer and make a run for it, but halfway through the reading of the clue, Brittany grabbed Kevin’s arm and screamed "I know it!" and they took off.

The clue directed them to One If By Land Two If By Sea, a former carriage house and "THE place to propose," Brittany remembered from watching an episode of Millionaire Matchmaker.

Brittany and Kevin almost missed out when they first ran into a bar next to the restaurant in their excitement, but this is how their Diamond Dash ended: